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From Racemates to Single Enantiomers – Chiral Synthetic Drugs over the last 20 Years

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Novel Optical Resolution Technologies

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 269))

Abstract

Before 1985, most chiral drugs newly introduced annually to the market were racemates and only three to five drugswere launched yearly as single enantiomers. Since then,the situation has changed dramatically, with racemates being introduced only rarely to the market. In 2004,all the new synthetic drugs (13 in the world) were launched as single enantiomers.

This article summarizes the change of chiral drugs in the last two decades from racemates to singleenantiomers and outlines the structural features of these new drugs and the manufacturing technologies appliedto introduce chirality to them – chirality pool, various types of resolutions and asymmetric syntheses,of which the new technologies developed recently are highlighted.

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Abbreviations

ACE:

Angiotensin converting enzyme

CMV:

Cytomegalovirus

CNS:

Central nervous system

CSA:

10-Camphorsulfonic acid

DBTA:

O,O′-Dibenzoyl-tartaricacid

DTTA:

O,O′-Ditoluoyl-tartaricacid

HMG-CoA:

3-Hydroxy-3-methylglutaryl coenzyme A

IPA:

Isopropyl alcohol

MA:

Mandelic acid

MBA:

α-Methylbenzylamine

Mw:

Molecular weight

NCE:

New chemical entitiy

NCS:

N-Chlorosuccinimide

NK1:

Neurokinin 1

SMB:

Simulated moving bed

TA:

Tartaric acid

p-TSA:

p-Toluenesulfonic acid

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Authors and Affiliations

  1. Ex-Director of R&D Division, Yamakawa Chemical Industry Co., Ltd, Kitaibaraki, 319-1541, Ibaraki, Japan

    Hisamichi Murakami

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  1. Hisamichi Murakami
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Correspondence to Hisamichi Murakami .

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Kenichi Sakai Noriaki Hirayama Rui Tamura

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© 2006 Springer-Verlag Berlin Heidelberg

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Murakami, H. (2006). From Racemates to Single Enantiomers – Chiral Synthetic Drugs over the last 20 Years. In: Sakai, K., Hirayama, N., Tamura, R. (eds) Novel Optical Resolution Technologies. Topics in Current Chemistry, vol 269. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2006_072

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